Tetrahydrofuran → sodium (6R,7R)-3-(hydroxymethyl)-8-oxo-7-[[(2Z)-2-[2-(tritylamino)-1,3-thiazol-4-yl]-2-trityloxyiminoacetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

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Reaction Steps

In 20 ml of water is suspended 260 mg of 7β-amino-3-hydroxymethyl-3-cephem-4-carboxylic acid, and with ice-cooling and stirring, the suspension is adjusted to pH 7.0 with 1N-aqueous sodium hydroxide solution. After dissolution, 930 mg of 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(trityloxyimino)acetic acid benzothiazol-2-ylthio ester, 20 ml of tetrahydrofuran, 20 ml of dioxane and 10 ml of acetonitrile are added and the mixture is stirred at room temperature for 38 hours. The reaction mixture is filtered and the filtrate is concentrated under reduced pressure. The residue is dissolved in 30 ml of tetrahydrofuran and the solution is subjected to silica gel (100 g) column chromatography. After the column is washed with acetonitrile (500 ml) and acetonitrile-water (19:1, 200 ml; 9:1, 200 ml), elution is carried out with 300 ml of acetonitrile-water (17:3). The eluate is concentrated under reduced pressure and the concentrate is freeze-dried to give 420 mg of sodium 7β-[2-(2-tritylaminothiazol-4-yl)-(Z)-2-(trityloxyimino)acetamido]-3-hydroxymethyl-3-cephem-4-carboxylate as light yellow powders.

Provenance & Evidence